EP3763804B1 - Liquid anti-friction composition - Google Patents
Liquid anti-friction composition Download PDFInfo
- Publication number
- EP3763804B1 EP3763804B1 EP20184826.4A EP20184826A EP3763804B1 EP 3763804 B1 EP3763804 B1 EP 3763804B1 EP 20184826 A EP20184826 A EP 20184826A EP 3763804 B1 EP3763804 B1 EP 3763804B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- friction
- friction composition
- acid
- liquid anti
- acid component
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000000203 mixture Substances 0.000 title claims description 69
- 239000007788 liquid Substances 0.000 title claims description 38
- 239000002253 acid Substances 0.000 claims description 36
- 150000002148 esters Chemical class 0.000 claims description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 18
- 229930195729 fatty acid Natural products 0.000 claims description 18
- 239000000194 fatty acid Substances 0.000 claims description 18
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- 238000005886 esterification reaction Methods 0.000 claims description 15
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 7
- 235000011037 adipic acid Nutrition 0.000 claims description 6
- 239000001361 adipic acid Substances 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 4
- 230000001050 lubricating effect Effects 0.000 claims description 3
- 239000000047 product Substances 0.000 description 23
- 238000012360 testing method Methods 0.000 description 16
- 230000000694 effects Effects 0.000 description 8
- 239000010705 motor oil Substances 0.000 description 8
- 238000005265 energy consumption Methods 0.000 description 7
- 239000002199 base oil Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 231100000241 scar Toxicity 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical group OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 229920000223 polyglycerol Polymers 0.000 description 4
- JYKSTGLAIMQDRA-UHFFFAOYSA-N tetraglycerol Chemical group OCC(O)CO.OCC(O)CO.OCC(O)CO.OCC(O)CO JYKSTGLAIMQDRA-UHFFFAOYSA-N 0.000 description 4
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 101100332655 Arabidopsis thaliana ECA2 gene Proteins 0.000 description 3
- 102000017703 GABRG2 Human genes 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000003831 antifriction material Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- -1 poly(hydroxystearic acid) Polymers 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 238000013517 stratification Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
- C10M129/78—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids
- C10M129/80—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids, hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M105/00—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound
- C10M105/08—Lubricating compositions characterised by the base-material being a non-macromolecular organic compound containing oxygen
- C10M105/32—Esters
- C10M105/42—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids
- C10M105/44—Complex esters, i.e. compounds containing at least three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compound: monohydroxy compounds, polyhydroxy compounds, monocarboxylic acids, polycarboxylic acids and hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
- C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
- C10M2203/102—Aliphatic fractions
- C10M2203/1025—Aliphatic fractions used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/287—Partial esters
- C10M2207/289—Partial esters containing free hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
- C10M2207/28—Esters
- C10M2207/30—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids
- C10M2207/302—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups
- C10M2207/3025—Complex esters, i.e. compounds containing at leasst three esterified carboxyl groups and derived from the combination of at least three different types of the following five types of compounds: monohydroxyl compounds, polyhydroxy xompounds, monocarboxylic acids, polycarboxylic acids or hydroxy carboxylic acids derived from the combination of monocarboxylic acids, dicarboxylic acids and dihydroxy compounds only and having no free hydroxy or carboxyl groups used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
- C10N2020/01—Physico-chemical properties
- C10N2020/02—Viscosity; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/02—Pour-point; Viscosity index
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/06—Oiliness; Film-strength; Anti-wear; Resistance to extreme pressure
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/54—Fuel economy
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/70—Soluble oils
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/25—Internal-combustion engines
Definitions
- the present disclosure relates to an anti-friction composition, and more particularly to a liquid anti-friction composition including an ester product.
- PCT International Patent Publication No. WO 2017/016825 A1 discloses a lubricating oil composition including a polyglycerol partial ester that is obtained by subjecting a polyglycerol mixture, polyfunctional carboxylic acid, fatty acids, and poly(hydroxystearic acid) to an esterification reaction.
- the polyglycerol partial ester has a hydroxyl value that ranges from 50 mg KOH/g to 180 mg KOH/g.
- the polyglycerol mixture has an esterification degree that ranges between 30% and 75% of hydroxyl (-OH) group, and an average condensation degree that ranges from 3 to 6.
- the polyfunctional carboxylic acid is an aliphatic dicarboxylic acid.
- the fatty acids are saturated or unsaturated, linear or branched fatty acids having 8 to 22 carbon atoms.
- the lubricating oil composition disclosed in the aforesaid PCT patent application is capable of lubricating an engine, and reducing friction and energy loss in the engine, thereby achieving energy saving effect.
- an anti-friction composition with improved friction reducing performance so as to satisfy the requirements of various industries.
- an object of the present disclosure is to provide a liquid anti-friction composition, which can alleviate at least one of the drawbacks of the prior art.
- the liquid anti-friction composition includes an ester product having a number average molecular weight that is greater than 3800 g/mol.
- the ester product is obtained by subjecting a mixture that includes diglycerol, a monobasic acid component, and a dibasic acid component to an esterification reaction.
- the monobasic acid component includes at least one C 14 -C 24 branched chain fatty acid.
- the present disclosure provides a liquid anti-friction composition including an ester product, which is obtained by subjecting a mixture that includes diglycerol, a monobasic acid component, and a dibasic acid component to an esterification reaction.
- the monobasic acid component includes at least one C 14 -C 24 branched chain fatty acid.
- the ester product has a number average molecular weight that is greater than 3800 g/mol.
- the number average molecular weight of the ester product ranges from 4200 g/mol to 6000 g/mol, such that the liquid anti-friction composition may have a more improved anti-friction effect (i.e., more reduced friction or more enhanced lubricity).
- the ester product has an esterification degree of greater than 80%, such that the liquid anti-friction composition may have a more enhanced anti-friction effect.
- the diglycerol is a commercial product available from manufacturers such as Solvay S.A., Spiga Nord S.p.A., Lonza Group AG, Sakamoto Orient Chemicals Corporation.
- the monobasic acid component further includes at least one straight chain C 14 -C 24 fatty acid.
- the C 14 -C 24 branched and/or straight chain fatty acid may be a C 14 -C 24 saturated fatty acid or a C 14 -C 24 unsaturated fatty acid.
- Exemplary C 14 -C 24 saturated fatty acids suitable for use in this disclosure may include, but are not limited to, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and combinations thereof.
- Exemplary C 14 -C 24 unsaturated fatty acids suitable for use in this disclosure may include, but are not limited to, oleic acid, palmitoleic acid, linoleic acid, linolenic acid, erucic acid, and combinations thereof.
- the monobasic acid component includes at least one C 18 fatty acid.
- the at least one C 18 fatty acid is present in an amount that is greater than 70 wt% based on 100 wt% of the monobasic acid component, such that the liquid anti-friction composition may have more improved compatibility with a base oil of an engine.
- the monobasic acid component includes at least one C 16 fatty acid and at least one C 18 fatty acid.
- the monobasic acid component may include several different C 16 fatty acids and several different C 18 fatty acids.
- the monobasic acid component is present in an amount that ranges from 60 wt% to 85 wt% based on 100 wt% of the mixture.
- the dibasic acid component includes at least one C 6 -C 10 dibasic acid.
- the C 6 -C 10 dibasic acid may include, but are not limited to, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid.
- the dibasic acid component is present in an amount that ranges from 10 wt% to 20 wt% based on 100 wt% of the mixture.
- the esterification reaction is conducted at a temperature that ranges from 160°C to 240°C.
- the liquid anti-friction composition has a kinematic viscosity at 100°C that is greater than 500 mm 2 /s (500 cSt), as determined according to ASTM D445.
- the esterification reaction may be further conducted in the presence of a catalyst.
- a catalyst suitable for use in this disclosure may include, but are not limited to, stannous oxalate (SnC 2 O 4 ), stannous oxide (SnO), tetrabutyl titanate, titanium tetraisopropanolate, methanesulfonic acid, and combinations thereof.
- the present disclosure also provides a method for lubricating an engine that includes a turbocharger and/or reducing friction in the engine, including applying the above-mentioned liquid anti-friction composition to the engine.
- a mixture including diglycerol (Manufacturer: Sakamoto Orient Chemicals Corporation), adipic acid (serving as a dibasic acid component), and a monobasic acid component in a specified amount and wt% as shown in Table 1 below, was subjected to an esterification reaction at a temperature of 220 ⁇ 5°C, so as to obtain an ester product in a liquid form serving as an anti-friction composition of E1.
- the monobasic acid component used in the mixture includes several different C 16 fatty acids and several different C 18 fatty acids, and the C 18 fatty acids are present in an amount of 80 ⁇ 5 wt% based on 100 wt% of the monobasic acid component. At least one of the abovementioned fatty acids is a branched chain fatty acid.
- the procedures for preparing a respective one of the anti-friction compositions of CE2 to CE4 were similar to those of E1, except that diglycerol was replaced with tetraglycerol in CE2, and was replaced with pentaerythritol in CE3 and CE4.
- the amount and wt% of the tetraglycerol, pentaerythritol, adipic acid, and monobasic acid component used in CE2 to CE4 are shown in Table 1 below.
- a commercially available anti-friction agent (Manufacturer: Croda International PLC; Model No.: PerfadTM 3057) was directly utilized as CE5.
- the kinematic viscosity for each of the anti-friction compositions of E1 and CE1 to CE5 was measured according to the procedures set forth in ASTM D445 at 100°C using a viscometer (Manufacturer: Anton Paar Co. Ltd.; Model No.: SVM 3000), and the viscosity index thereof was calculated based on the measured kinematic viscosity. 2.
- Number average molecular weight 1 g of the anti-friction composition of the respective one of E1, CE1 to CE4, and CE6 to CE6 was dissolved in tetrahydrofuran, and then was subjected to a liquid chromatography analysis (column type: ACQUITY APCTM from Waters Corporation; mobile phase: tetrahydrofuran; flow rate: 0.5 mL/min; temperature: 40°C) with polystyrene as a standard, so as to determine the number average molecular weight of the ester product in the anti-friction composition.
- the hydroxyl value (unit: mg KOH/g) was determined through acetic anhydride acetylation according to the procedures set forth in ASTM E222.
- the oxidative stability was evaluated by measuring an oxidation onset temperature of the anti-friction composition of the respective one of E1, CE3 and CE5 using a differential scanning calorimeter analyzer (Manufacturer: TA Instruments; Model No.: Q20) according to the procedures set forth in ASTM E2009-08(2014 ), which was conducted under an atmosphere of oxygen that had a pressure of 500 psi and a flow rate of 50 mL/min, and a temperature that increased from room temperature up to 250°C with a heating rate of 5°C/min.
- a differential scanning calorimeter analyzer Manufacturer: TA Instruments; Model No.: Q20
- the ester product of E1 and CE2 As shown in Table 1, although the number average molecular weights of both the ester products of the anti-friction compositions of E1 and CE2 are greater than 3800 g/mol, the ester product of E1, which was formed by a reaction mixture including diglycerol, has a smaller scar diameter as compared to that of the ester product of CE2 which was formed by a reaction mixture including tetraglycerol. Although the ester products of CE6 and CE8 also have the number average molecular weight greater than 3800 g/mol and were obtained from a reaction mixture including diglycerol, the resultant anti-friction compositions are not in a liquid form.
- ester products of the anti-friction compositions of CE3 and CE4, each of which was formed by a reaction mixture that includes pentaerythritol have a number average molecular weight that is smaller than 3800 g/mol and a greater scar diameter as compared to those of the ester product of the anti-friction composition of E1.
- the anti-friction composition of E1 has a smaller scar diameter and exhibits improved oxidative stability.
- ester product of the anti-friction composition of this disclosure which is in a liquid form, and which is obtained from a reaction mixture including diglycerol and has the number average molecular weight of greater than 3800 g/mol, exhibits an excellent anti-friction effect.
- 1 wt% of the anti-friction composition of the respective one of E1, CE1, CE2, and CE5 was blended with 99 wt% of an engine oil SAE OW16, so as to obtain test samples of AE1 and CAE1 to CAE3.
- 1 wt% of the anti-friction composition of the respective one of E1 and CE5 was blended with 99 wt% of an engine oil SAE 0W40, so as to obtain test samples of AE2 and CAE4.
- 100 wt% of the engine oil 0W16 and 100 wt% of the engine oil 0W40 were used as test samples of CAE5 and CAE6, respectively.
- test samples of AE1, CAE1 to CAE3, and CAE5 were subjected to a wear test using a block-on-ring test machine (Manufacturer: Reichert, Inc.), which was conducted under a temperature of 120°C, a load of 20 ⁇ 0.2 kg, and a rotation speed ranging from 0 rpm to 400 rpm with an increasing rate of 200 rpm/min, so as to measure the friction coefficient and thereby obtain a Stribeck curve for each test sample.
- the Stribeck curves of the test samples of AE1, CAE1 to CAE3, and CAE5 were integrated to obtain corresponding energy consumption values.
- test samples of AE2, CAE4 and CAE6 were also subjected to a wear test similar to the above wear test, except that a rotation speed of 400 rpm was applied for a time period of 1 hour, and a friction area (mm 2 ) was determined.
- the anti-friction compositions of CE1, CE2, and CE5 respectively used in CAE1, CAE2 and CAE3 can reduce the energy consumption values from 101.3 J (i.e., shown by the engine oil 0W16 of CAE5) to a range from 99.1 J to 100.4 J
- the energy consumption value of AE1, which contains the anti-friction composition of E1 is significantly reduced to 95.4 J.
- the results indicate that the anti-friction composition of this disclosure demonstrates an enhanced improvement in energy use efficiency, and thus has an excellent energy-saving effect.
- the friction area determined in AE2 is significantly lower, indicating that the anti-friction composition of E1 has an improved anti-friction effect, and is capable of effectively improving the lubricity of engine oil.
- the liquid anti-friction composition of the present disclosure is conferred with an excellent anti-friction effect. Therefore, the liquid anti-friction composition of the present disclosure is expected to be useful for improving the lubricity of an engine oil, so as to reduce the energy consumption of an internal combustion engine, thereby achieving an energy-saving effect.
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Description
- The present disclosure relates to an anti-friction composition, and more particularly to a liquid anti-friction composition including an ester product.
-
PCT International Patent Publication No. WO 2017/016825 A1 discloses a lubricating oil composition including a polyglycerol partial ester that is obtained by subjecting a polyglycerol mixture, polyfunctional carboxylic acid, fatty acids, and poly(hydroxystearic acid) to an esterification reaction. The polyglycerol partial ester has a hydroxyl value that ranges from 50 mg KOH/g to 180 mg KOH/g. The polyglycerol mixture has an esterification degree that ranges between 30% and 75% of hydroxyl (-OH) group, and an average condensation degree that ranges from 3 to 6. The polyfunctional carboxylic acid is an aliphatic dicarboxylic acid. The fatty acids are saturated or unsaturated, linear or branched fatty acids having 8 to 22 carbon atoms. - The lubricating oil composition disclosed in the aforesaid PCT patent application is capable of lubricating an engine, and reducing friction and energy loss in the engine, thereby achieving energy saving effect. However, there is still a need to develop an anti-friction composition with improved friction reducing performance so as to satisfy the requirements of various industries.
- Therefore, an object of the present disclosure is to provide a liquid anti-friction composition, which can alleviate at least one of the drawbacks of the prior art.
- The liquid anti-friction composition includes an ester product having a number average molecular weight that is greater than 3800 g/mol. The ester product is obtained by subjecting a mixture that includes diglycerol, a monobasic acid component, and a dibasic acid component to an esterification reaction. The monobasic acid component includes at least one C14-C24 branched chain fatty acid.
- For the purpose of this specification, it will be clearly understood that the word "comprising" means "including but not limited to", and that the word "comprises" has a corresponding meaning.
- Unless otherwise defined, all technical and scientific terms used herein have the meaning commonly understood by a person skilled in the art to which this disclosure belongs. One skilled in the art will recognize many methods and materials similar or equivalent to those described herein, which could be used in the practice of this disclosure. Indeed, this disclosure is in no way limited to the methods and materials described.
- The present disclosure provides a liquid anti-friction composition including an ester product, which is obtained by subjecting a mixture that includes diglycerol, a monobasic acid component, and a dibasic acid component to an esterification reaction. The monobasic acid component includes at least one C14-C24 branched chain fatty acid. The ester product has a number average molecular weight that is greater than 3800 g/mol.
- In certain embodiments, the number average molecular weight of the ester product ranges from 4200 g/mol to 6000 g/mol, such that the liquid anti-friction composition may have a more improved anti-friction effect (i.e., more reduced friction or more enhanced lubricity).
- In certain embodiments, the ester product has an esterification degree of greater than 80%, such that the liquid anti-friction composition may have a more enhanced anti-friction effect.
- The diglycerol is a commercial product available from manufacturers such as Solvay S.A., Spiga Nord S.p.A., Lonza Group AG, Sakamoto Orient Chemicals Corporation.
- In certain embodiments, the monobasic acid component further includes at least one straight chain C14-C24 fatty acid. The C14-C24 branched and/or straight chain fatty acid may be a C14-C24 saturated fatty acid or a C14-C24 unsaturated fatty acid. Exemplary C14-C24 saturated fatty acids suitable for use in this disclosure may include, but are not limited to, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, and combinations thereof. Exemplary C14-C24 unsaturated fatty acids suitable for use in this disclosure may include, but are not limited to, oleic acid, palmitoleic acid, linoleic acid, linolenic acid, erucic acid, and combinations thereof.
- In certain embodiments, the monobasic acid component includes at least one C18 fatty acid. The at least one C18 fatty acid is present in an amount that is greater than 70 wt% based on 100 wt% of the monobasic acid component, such that the liquid anti-friction composition may have more improved compatibility with a base oil of an engine.
- In other embodiments, the monobasic acid component includes at least one C16 fatty acid and at least one C18 fatty acid. For example, the monobasic acid component may include several different C16 fatty acids and several different C18 fatty acids.
- In order to obtain the ester product having the number average molecular weight that is greater than 3800 g/mol and to avoid the formation of a gel-like or non-liquid cross-linked ester product, in certain embodiments, the monobasic acid component is present in an amount that ranges from 60 wt% to 85 wt% based on 100 wt% of the mixture.
- In certain embodiments, the dibasic acid component includes at least one C6-C10 dibasic acid. Examples of the C6-C10 dibasic acid may include, but are not limited to, adipic acid, pimelic acid, suberic acid, azelaic acid, and sebacic acid.
- In order to obtain the ester product having the number average molecular weight that is greater than 3800 g/mol and to avoid the formation of a gel-like or non-liquid cross-linked ester product, in certain embodiments, the dibasic acid component is present in an amount that ranges from 10 wt% to 20 wt% based on 100 wt% of the mixture.
- In certain embodiments, the esterification reaction is conducted at a temperature that ranges from 160°C to 240°C.
- In certain embodiments, the liquid anti-friction composition has a kinematic viscosity at 100°C that is greater than 500 mm2/s (500 cSt), as determined according to ASTM D445.
- In addition, the esterification reaction may be further conducted in the presence of a catalyst. Examples of the catalyst suitable for use in this disclosure may include, but are not limited to, stannous oxalate (SnC2O4), stannous oxide (SnO), tetrabutyl titanate, titanium tetraisopropanolate, methanesulfonic acid, and combinations thereof.
- The present disclosure also provides a method for lubricating an engine that includes a turbocharger and/or reducing friction in the engine, including applying the above-mentioned liquid anti-friction composition to the engine.
- The present disclosure will be further described by way of the following examples. However, it should be understood that the following examples are intended solely for the purpose of illustration and should not be construed as limiting the present disclosure in practice.
- A mixture, including diglycerol (Manufacturer: Sakamoto Orient Chemicals Corporation), adipic acid (serving as a dibasic acid component), and a monobasic acid component in a specified amount and wt% as shown in Table 1 below, was subjected to an esterification reaction at a temperature of 220±5°C, so as to obtain an ester product in a liquid form serving as an anti-friction composition of E1. The monobasic acid component used in the mixture includes several different C16 fatty acids and several different C18 fatty acids, and the C18 fatty acids are present in an amount of 80±5 wt% based on 100 wt% of the monobasic acid component. At least one of the abovementioned fatty acids is a branched chain fatty acid.
- The procedures for preparing a respective one of the anti-friction compositions of CE1 and CE6 to CE8 were similar to those of E1, except for differences in the amount and wt% of the diglycerol, adipic acid, and monobasic acid component applied in CE1 and CE6 to CE8, which are shown in Table 1 below.
- The procedures for preparing a respective one of the anti-friction compositions of CE2 to CE4 were similar to those of E1, except that diglycerol was replaced with tetraglycerol in CE2, and was replaced with pentaerythritol in CE3 and CE4. The amount and wt% of the tetraglycerol, pentaerythritol, adipic acid, and monobasic acid component used in CE2 to CE4 are shown in Table 1 below.
- A commercially available anti-friction agent (Manufacturer: Croda International PLC; Model No.: Perfad™ 3057) was directly utilized as CE5.
- The kinematic viscosity for each of the anti-friction compositions of E1 and CE1 to CE5 was measured according to the procedures set forth in ASTM D445 at 100°C using a viscometer (Manufacturer: Anton Paar Co. Ltd.; Model No.: SVM 3000), and the viscosity index thereof was calculated based on the measured kinematic viscosity. 2. Number average molecular weight 1 g of the anti-friction composition of the respective one of E1, CE1 to CE4, and CE6 to CE6 was dissolved in tetrahydrofuran, and then was subjected to a liquid chromatography analysis (column type: ACQUITY APC™ from Waters Corporation; mobile phase: tetrahydrofuran; flow rate: 0.5 mL/min; temperature: 40°C) with polystyrene as a standard, so as to determine the number average molecular weight of the ester product in the anti-friction composition.
-
- A=esterification degree
- B=hydroxyl value of diglycerol
- C=hydroxyl value of the ester product of the respective anti-friction composition
- The hydroxyl value (unit: mg KOH/g) was determined through acetic anhydride acetylation according to the procedures set forth in ASTM E222.
- In order to determine the compatibility with a base oil, 1 g of the anti-friction composition of the respective one of E1, CE1 to CE4, and CE7 was blended with 99 g of a base oil (Manufacturer: SK Lubricants; Model No.: Yubase 4) at 80°C, and the resultant blend was then left to stand at room temperature for 24 hours, so as to visually observe whether there was presence of stratification, precipitation or fogging in the resultant blend.
- 1 wt% of the anti-friction composition of the respective one of E1 and CE2 to CE4 was mixed with 99 wt% of a base oil (Manufacturer: SK Lubricants; Model No. : Yubase 4), so as to obtain test samples of E1 and CE2 to CE4. An anti-friction property (i.e., wear preventive characteristics) was evaluated by measuring a scar diameter of the respective test sample using a four-ball wear test machine according to the procedures set forth in ASTM D4172-94 (2016), which was conducted under a temperature of 75°C, a rotation speed of 1200 rpm, and a load of 40±0.2 kg for 1 hour.
- The oxidative stability was evaluated by measuring an oxidation onset temperature of the anti-friction composition of the respective one of E1, CE3 and CE5 using a differential scanning calorimeter analyzer (Manufacturer: TA Instruments; Model No.: Q20) according to the procedures set forth in ASTM E2009-08(2014), which was conducted under an atmosphere of oxygen that had a pressure of 500 psi and a flow rate of 50 mL/min, and a temperature that increased from room temperature up to 250°C with a heating rate of 5°C/min.
Table 1 Anti-friction composition E1 CE1 CE2 CE3 CE4 CE5 CE6 CE7 CE8 Reaction mixture (wt%) Diglycerol 218 g (20.2) 225 g (21) 0 0 0 - 275 g (25.1) 190 g (17.8) 235 g (21.7) Tetraglycerol 0 0 272 g (25.5) 0 0 - 0 0 0 Pentaerythritol 0 0 0 209 g (19.2) 229 g (21.2) - 0 0 0 Dibasic acid component Adipic acid 167 g (15.4) 116 (10.9) 110 g (10.3) 187 g (17.2) 164 g (15.2) - 220 g (20.1) 85 g (8.0) 200 g (18.4) Monobasic acid component 696 g (64.4) 728 g (68.1) 684 g (64.2) 691 g (63.6) 688 g (63.6) - 600 g (54.8) 790 g (74.2) 650 g (59.9) Property evaluation Kinematic viscosity at 100°C (cSt) 550 130 150 880 160 221 n.d. n.d. n.d. Viscosity index 230 166 151 234 125 146 n.d. n.d. n.d. Number average molecular weight 4200 1500 5500 3800 2000 n.d. 4500 1500 8400 Esterification degree (%) 85 72 74 78 69 n.d. 74 80 85 State of matter Liquid Liquid Liquid Liquid Liquid Liquid Gel-like Liquid Gel-like Base oil compatibility Yes Yes Yes Yes Yes n.d. n.d. Yes n.d. Scar diameter (mm) 0.528 n.d. 0.578 0.600 0.605 0.623 n.d. n.d. n.d. Oxidation onset temperature (°C) 172 n.d. n.d. 171 n.d. 155 n.d. n.d. n.d. "-": not applicable; "n.d.": not determined - As shown in Table 1, although the number average molecular weights of both the ester products of the anti-friction compositions of E1 and CE2 are greater than 3800 g/mol, the ester product of E1, which was formed by a reaction mixture including diglycerol, has a smaller scar diameter as compared to that of the ester product of CE2 which was formed by a reaction mixture including tetraglycerol. Although the ester products of CE6 and CE8 also have the number average molecular weight greater than 3800 g/mol and were obtained from a reaction mixture including diglycerol, the resultant anti-friction compositions are not in a liquid form. In addition, the ester products of the anti-friction compositions of CE3 and CE4, each of which was formed by a reaction mixture that includes pentaerythritol, have a number average molecular weight that is smaller than 3800 g/mol and a greater scar diameter as compared to those of the ester product of the anti-friction composition of E1. As compared to the commercially available anti-friction agent of CE5, the anti-friction composition of E1 has a smaller scar diameter and exhibits improved oxidative stability.
- These results indicate that the ester product of the anti-friction composition of this disclosure, which is in a liquid form, and which is obtained from a reaction mixture including diglycerol and has the number average molecular weight of greater than 3800 g/mol, exhibits an excellent anti-friction effect.
- 1 wt% of the anti-friction composition of the respective one of E1, CE1, CE2, and CE5 was blended with 99 wt% of an engine oil SAE OW16, so as to obtain test samples of AE1 and CAE1 to CAE3. In addition, 1 wt% of the anti-friction composition of the respective one of E1 and CE5 was blended with 99 wt% of an engine oil SAE 0W40, so as to obtain test samples of AE2 and CAE4.
- 100 wt% of the engine oil 0W16 and 100 wt% of the engine oil 0W40 were used as test samples of CAE5 and CAE6, respectively.
- Each of the test samples of AE1, CAE1 to CAE3, and CAE5 was subjected to a wear test using a block-on-ring test machine (Manufacturer: Reichert, Inc.), which was conducted under a temperature of 120°C, a load of 20±0.2 kg, and a rotation speed ranging from 0 rpm to 400 rpm with an increasing rate of 200 rpm/min, so as to measure the friction coefficient and thereby obtain a Stribeck curve for each test sample. After that, the Stribeck curves of the test samples of AE1, CAE1 to CAE3, and CAE5 were integrated to obtain corresponding energy consumption values. The improvement in energy use efficiency for each of the test samples of AE1 and CAE1 to CAE3 relative to CAE5 was calculated using the following formula:
- A=improvement in energy use efficiency
- B=energy consumption value of CAE5
- C=energy consumption value of AE1, CAE1, CAE2 or CAE3
- On the other hand, the test samples of AE2, CAE4 and CAE6 were also subjected to a wear test similar to the above wear test, except that a rotation speed of 400 rpm was applied for a time period of 1 hour, and a friction area (mm2) was determined.
Table 2 AE1 AE2 CAE1 CAE2 CAE3 CAE4 CAE5 CAE 6 Engine oil 0W16 (wt%) 99 0 99 99 99 0 100 0 0W40 (wt%) 0 99 0 0 0 99 0 100 Anti-friction composition Examples E1 E1 - - - - - - Comparative Examples - - CE1 CE2 CE5 CE5 - - Amount (wt%) 1 1 1 1 1 1 - - Property evaluation Energy consumption (J) 95.4 n.d. 99.1 100.1 100.4 n.d. 101.3 n.d. Improvement in energy use efficiency (%) 5.82 n.d. 2.17 1.18 0.89 n.d. - n.d. Wear scar area (mm2) n.d. 0.48 n.d. n.d. n.d. 0.50 n.d. 0.52 "-": not applicable; "n.d.": not determined - As shown in Table 2, although the anti-friction compositions of CE1, CE2, and CE5 respectively used in CAE1, CAE2 and CAE3 can reduce the energy consumption values from 101.3 J (i.e., shown by the engine oil 0W16 of CAE5) to a range from 99.1 J to 100.4 J, the energy consumption value of AE1, which contains the anti-friction composition of E1, is significantly reduced to 95.4 J. The results indicate that the anti-friction composition of this disclosure demonstrates an enhanced improvement in energy use efficiency, and thus has an excellent energy-saving effect.
- In addition, as compared to the friction area determined in CAE4 (i.e., 0.50 mm2) and CAE6 (i.e., 0.52 mm2), the friction area determined in AE2 is significantly lower, indicating that the anti-friction composition of E1 has an improved anti-friction effect, and is capable of effectively improving the lubricity of engine oil.
- In summary, by inclusion of diglycerol in the mixture subjected to the esterification reaction, and by controlling the number average molecular weight of the resultant ester product to be greater than 3800 g/mol, the liquid anti-friction composition of the present disclosure is conferred with an excellent anti-friction effect. Therefore, the liquid anti-friction composition of the present disclosure is expected to be useful for improving the lubricity of an engine oil, so as to reduce the energy consumption of an internal combustion engine, thereby achieving an energy-saving effect.
- In the description above, for the purposes of explanation, numerous specific details have been set forth in order to provide a thorough understanding of the embodiments. It will be apparent, however, to one skilled in the art, that one or more other embodiments may be practiced without some of these specific details. It should also be appreciated that reference throughout this specification to "one embodiment," "an embodiment," an embodiment with an indication of an ordinal number and so forth means that a particular feature, structure, or characteristic may be included in the practice of the disclosure. It should be further appreciated that in the description, various features are sometimes grouped together in a single embodiment, figure, or description thereof for the purpose of streamlining the disclosure and aiding in the understanding of various inventive aspects, and that one or more features or specific details from one embodiment may be practiced together with one or more features or specific details from another embodiment, where appropriate, in the practice of the disclosure.
Claims (11)
- A liquid anti-friction composition, characterized by an ester product having a number average molecular weight that is greater than 3800 g/mol, and obtained by subjecting a mixture that includes diglycerol, a monobasic acid component, and a dibasic acid component to an esterification reaction, said monobasic acid component including at least one C14-C24 branched chain fatty acid.
- The liquid anti-friction composition as claimed in claim 1, characterized in that said monobasic acid component further includes at least one C14-C24 straight chain fatty acid.
- The liquid anti-friction composition as claimed in any one of claims 1 to 2, characterized in that said monobasic acid component includes at least one C18 fatty acid present in an amount that is greater than 70 wt% based on 100 wt% of said monobasic acid component.
- The liquid anti-friction composition as claimed in claim 3, characterized in that said monobasic acid component further includes at least one C16 fatty acid.
- The liquid anti-friction composition as claimed in any one of claims 1 to 4, characterized in that said dibasic acid component includes at least one C6-C10 dibasic acid.
- The liquid anti-friction composition as claimed in claim 5, characterized in that said C6-C10 dibasic acid is selected from the group consisting of adipic acid, pimelic acid, suberic acid, azelaic acid and sebacic acid.
- The liquid anti-friction composition as claimed in any one of claims 1 to 6, characterized in that said monobasic acid component is present in an amount that ranges from 60 wt% to 85 wt% based on 100 wt% of said mixture.
- The liquid anti-friction composition as claimed in any one of claims 1 to 7, characterized in that said dibasic acid component is present in an amount that ranges from 10 wt% to 20 wt% based on 100 wt% of said mixture.
- The liquid anti-friction composition as claimed in any one of claims 1 to 8, characterized in that said ester product has an esterification degree of greater than 80%.
- The liquid anti-friction composition as claimed in any one of claims 1 to 9, characterized in that said liquid anti-friction composition has a kinematic viscosity at 100°C that is greater than 500 mm2/s (500 cSt), as determined according to ASTM D445.
- A method for lubricating an engine and reducing friction in the engine, characterized by applying the liquid anti-friction composition as claimed in any one of claims 1 to 10 to the engine.
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IT1403272B1 (en) | 2010-12-20 | 2013-10-17 | Novamont Spa | COMPLEX OLIGOMERIC STRUCTURES |
SI2705125T1 (en) * | 2011-05-06 | 2018-04-30 | Oleon | Lubricity improver |
US20150113864A1 (en) | 2013-10-24 | 2015-04-30 | Basf Se | Use of a complex ester to reduce fuel consumption |
WO2017016825A1 (en) | 2015-07-24 | 2017-02-02 | Evonik Oil Additives Gmbh | Use of polyclycerin esters as friction modifiers in lubricant formulations |
WO2018042848A1 (en) | 2016-08-31 | 2018-03-08 | 富士フイルム株式会社 | Method for producing lubricant composition, and lubricant composition |
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2019
- 2019-07-10 TW TW108124303A patent/TWI793346B/en active
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2020
- 2020-04-03 CN CN202010257166.7A patent/CN112210418B/en active Active
- 2020-07-07 US US16/922,413 patent/US11186796B2/en active Active
- 2020-07-08 JP JP2020117617A patent/JP7032484B2/en active Active
- 2020-07-08 ES ES20184826T patent/ES2905076T3/en active Active
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ES2905076T3 (en) | 2022-04-07 |
JP2021014579A (en) | 2021-02-12 |
TW201940682A (en) | 2019-10-16 |
TWI793346B (en) | 2023-02-21 |
US20210009915A1 (en) | 2021-01-14 |
US11186796B2 (en) | 2021-11-30 |
EP3763804A1 (en) | 2021-01-13 |
CN112210418A (en) | 2021-01-12 |
JP7032484B2 (en) | 2022-03-08 |
CN112210418B (en) | 2022-11-15 |
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